This paper presents results of analyzing the second half of the 20th–early 21st century changes in lateral spatial structure of Larix sibirica Ledeb. population in the upper treeline ecotone located on the Rai-Iz massif (Polar Urals, Russia). The GIS layers characterizing distribution of Siberian larch trees and undergrowth together with their crowns was produced for a 7.32 square kilometer area based on aerial images recognition. Using statistical models, we assessed probabilities for assigning trees to age intervals of 1–10, 11–40, and 40+ years based on the average radius of tree crown projection. These maps and layer showing locations of trees that grew in the upper part of the ecotone, and died during the Little Ice Age, allow for assessing specifics of forest cover proliferation at different parts of upper treeline ecotone, and comparing current location of the trees with one from the past. The proposed method for probability-based recognition of Siberian larch tree generations in the upper treeline ecotone using average crown radius can be used to reconstruct time and spatial forest dynamics at the upper growth boundaries for time spans up to 100 years and more.